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Benzothiazole derivative and preparation method and application thereof

A technology of benzothiazole and methylbenzothiazole, which is applied in the field of heterocyclic compounds and fluorescent probes, can solve the problems of few reports and rare probes, and achieve reduced interference, good cell membrane penetration ability, and excellent anti-interference ability Effect

Active Publication Date: 2019-02-22
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the pH of subcellular compartments such as cytoplasmic matrix, nucleus, and mitochondria in a large number of cells is nearly neutral or weakly alkaline. There are not many reports on this kind of pH probes, especially the probes based on ratiometric fluorescence emission technology. is rare

Method used

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  • Benzothiazole derivative and preparation method and application thereof
  • Benzothiazole derivative and preparation method and application thereof
  • Benzothiazole derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Preparation of 1,6-(2-(benzothiazol-2-yl)vinyl)naphthalene-2-ol (BTNO):

[0027]

[0028] (1) 6-hydroxy-2-naphthaldehyde (10mmol, 1.7218g), 2-methylbenzothiazole (15mmol, 1.89mL), trimethylchlorosilane (50mmol, 6.40mL), 10mL CH2Cl2 mixed The solution was reacted in a high-pressure reactor at 105°C for 24h. The solvent was removed under reduced pressure, and the resulting solid was dissolved in water and washed with Na 2 CO 3 Adjust the pH of the solution to 6.0 with CH 2 Cl 2 extraction. Remove the solvent to obtain the product crude product;

[0029] (2) the product crude product is separated and purified through a silica gel column, v 乙酸乙酯 :v 正己烷 =1:6 was the eluent, and the product BTNO (1.58 g, 52%) was obtained as a reddish-brown solid. 1 H NMR(400MHz,DMSO)δ10.62(s,1H),10.34(s,1H),10.04(s,1H),9.97(s,1H),9.65(s,1H),8.43(s,1H) ,8.02(d,J=8.7Hz,2H),7.80(dd,J=18.1,8.5Hz,2H),7.21(d,J=8.4Hz,2H),7.02(s,1H). 13 C NMR (101MHz, d 6 -DMSO)δ197.80(s), 197.53(s), 1...

Embodiment 2

[0031] The BTNO concentration of Example 1 is maintained at 150 μM, and the pH value is adjusted with high-concentration and small-volume HCl and NaOH solutions in the DMSO / water (volume ratio is 2:1) system, and its absorption spectrum is recorded ( figure 1 ). With the decrease of pH value, the absorption peak at 385nm decreases gradually, the absorption peak at 321nm increases correspondingly, and there is an isosbestic point at 349nm. The color of the solution also changed from yellow to light green ( figure 2 ).

Embodiment 3

[0033] The BTNO concentration of Example 1 was kept at 10 μM, and the pH value was adjusted with high-concentration and small-volume HCl and NaOH solutions in the DMSO / water (volume ratio: 2:1) system, and the fluorescence emission was recorded at 349 nm as the excitation wavelength. spectrum( image 3 ). With the decrease of pH value, the fluorescence peak at 526nm weakens gradually, while the fluorescence peak at 456nm increases gradually. The color of the solution changed from green to blue ( Figure 4 ). Fitting F via the Boltzmann function 456nm / F 526nmValue vs. pH change curve, calculate pK a The value is 7.91±0.034 ( Figure 5 ), the pH response linear range is 7.00-9.50. The linear regression equation is F 456nm / F 526nm =2.13641-0.21119×pH, correlation coefficient R 2 =0.9995( Image 6 ).

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Abstract

The invention discloses a benzothiazole derivative and a preparation method and application thereof. The derivative is specifically named as 6-(2-(benzothiazolyl-2-yl)vinyl)naphthalene-2-phenol (BTNO). The preparation method comprises the following steps: dissolving 6-hydroxy-2-naphthaldehyde and 2-methylbenzothiazole in a very small amount of dichloromethane, adding trimethylchlorosilane and heating to obtain a crude product; removing a solvent from the crude product and conducting silica gel column separation to obtain a pure product. With decrease of the pH of BNTO from 11.50 to 4.00, fluorescence spectrums have blue shift and exhibit ratio fluorescence emission (F456nm / F526nm) characteristics. At the same time, the advantages of high sensitivity to pH response, good selectivity, high quantum yield and large Stokes displacement and the like can be achieved. In addition, the BTNO acts as a probe to mark cells by permeating cell membranes and can be used for monitoring pH fluctuationswithin the scope of cytoplasm.

Description

technical field [0001] The invention relates to a heterocyclic compound and a fluorescent probe, specifically a benzothiazole derivative (BTNO) and a preparation method thereof, as well as the application of the derivative in monitoring changes in cytoplasmic pH. Background technique [0002] Intracellular pH is one of the important parameters of cell metabolism and plays a very important role in various physiological and pathological processes of cells, such as regulation of enzyme activity, maintenance of protein shape, cell division and apoptosis, ion transport, endocytosis Function, cellular energy generation and conversion, membrane potential balance and information transmission, etc. At the same time, studies have shown that the growth and metastasis of cancer (tumor cells), multidrug resistance, Parkinson's disease, Alzheimer's disease and other diseases are closely related to abnormal intracellular pH. Therefore, real-time and accurate monitoring of intracellular pH...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/64C09K11/06G01N21/64
CPCG01N21/6486C09K11/06C07D277/64C09K2211/1011C09K2211/1037
Inventor 林博樊丽贾晶黄文成双少敏董川
Owner SHANXI UNIV
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